My most disappointing destination was San Francisco, by far. It's probably the most beautiful city to drive into. High hopes driving in after a trek from Portland down the highway.
The trash and homeless were incredible. Literally stepping over homeless with better shoes than me coming out of our hotel(which was $700/nt luxury I found in a top 10 romantic list)
Nearly every restaurant, bar, shop we went to, we'd ask about the neighborhood or where to head to next and most didn't know the neighborhood(as far as what places are like) because no one can afford to live there and they're all from Oakland, working in San Fran.
Everything seemed so disassociated and cold.